“Tell me about your game,” Spiegel said. Sebastian flopped into the chair and handed her his notepad, where he’d recorded all the moves for both players in the game.

Sebastian explained that the other guy was simply better. “He had good skills,” he said. “Good strategies.”

And this is the point where many of us would simply say something along the lines of “did you do your best?,” in which case the likely response is “Yes.” Everyone is at least let off the hook. The teacher for ensuring students try their best, the student for having lost to someone better. Spiegel did not take this approach.

The most critical missing piece, Randolph explained as we sat in his office last fall, is character — those essential traits of mind and habit that were drilled into him at boarding school in England and that also have deep roots in American history. “Whether it’s the pioneer in the Conestoga wagon or someone coming here in the 1920s from southern Italy, there was this idea in America that if you worked hard and you showed real grit, that you could be successful,” he said. “Strangely, we’ve now forgotten that. People who have an easy time of things, who get 800s on their SAT’s, I worry that those people get feedback that everything they’re doing is great. And I think as a result, we are actually setting them up for long-term failure. When that person suddenly has to face up to a difficult moment, then I think they’re screwed, to be honest. I don’t think they’ve grown the capacities to be able to handle that.”